History • Architecture • Food • Beer

Experience Winchester VA Like Never Before

Discover Winchester one step, sip, bite at a time!

Explore the city’s unique and thriving food scene on our downtown Winchester walking mall food tours. Your experienced guide will introduce you to great local dishes and drinks while sharing stories about Winchester’s rich history and architecture.

Self Guided Historic Food Tour

Explore Winchester in this one of a kind historic food tour where you’ll learn about the founding events of Winchester, local architecture, and visit 5-6 restaurants. 

Fri, Sat, Sun
$25 per group

    positive review  Misty and Anthony were great hosts of this informative walking/eating tour of historic downtown Winchester. Hideaway Cafe amazing tea and coffee as well as tasty sandwiches. Delightful experience at Fellowship of the Sip to include chickpea scramble, spinach quiche. Off to Benny’s for delish pizza and socializing finishing the tour with some out of this world pumpkin spice latte and treats from Moe’s. Such a mouth watering taste bud adventure as well as some historical tie bits. Highly recommend this to anyone.

    Christie Brown Arnold Avatar Christie Brown Arnold
    September 11, 2018

    positive review  The tour guide and all the people at the restaurants we stopped at were so nice and we definitely got our fill's worth!

    Emily Gallery Avatar Emily Gallery
    May 12, 2019

    positive review  We had such a good time touring with Anthony and Misty on a rainy Sunday afternoon doing the History & Hops tour! We stopped at four places, and learned about the breweries, the beer, and a bit of Winchester history as well. They had a good relationship with each of the establishments and really catered to us in every way - from recommending beers to our palettes, taking our orders, and cleaning up afterwards, it was really above and beyond what you would expect from your tour guides. They are great conversationalists who will feel more like fast friends by the time your tour has ended. We will definitely try the Food tour that they offer the next time we are in Winchester for the holidays!

    Emmy Gottschalk Avatar Emmy Gottschalk
    December 30, 2019